Growing To $500M AUM With An Evergreen HNW Client Service Calendar For Evergreen Fees: #FASuccess Ep 470 With Debra Taylor

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Resources Featured In This Episode:

• Debra Taylor: Website | LinkedIn
• Carson Wealth Annual Service Calendar – Download (PDF)
• Kitces Report: How Financial Planners Actually Do Financial Planning
• Implementing Client Meeting Surges To Boost Advisor Productivity And Systematize Client Value
• Holistiplan

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Full Transcript:

Michael: Welcome, Debbie Taylor, to the "Financial Advisor Success" podcast.

Debra: Hi.

Michael: I'm really excited to have you join us today and to get to talk about and nerd out a little bit on proactive tax planning with clients. I find, we're seeing it just on the rise across the industry. Our Kitces research studies, we see rising adoption of tax planning, although to be fair, it was pretty high already. A lot more firms doing in-house tax preparation, almost one in six independent firms bringing tax prep in-house for at least some clients. And then this explosive growth of the tax planning platform software, like Holistiplan and FP Alpha. But it is different. I find for a lot of us, planning is ultimately kind of reactive. After the initial plan, we monitor and say, "If anything changes in your financial life, please call us, and we'll help." Some of us try to be more proactive. We schedule more check-in meetings with our top clients to meet them more frequently to see if there's anything that's changed in their life that we can help with.

But tax planning, to me, is really unique because it has this very natural annual cadence, given the annual tax filing cycle. And it's so tangible to clients. It's not a, "Trust me, if you have these diligent savings habits, you'll totally thank me in 30 years when you're retired." It's more of a, "I saved you $3,722 in taxes this year. There it is. I can point to the line number on your tax return." And, Debbie, I know you have lived this deeply as a CPA-turned-financial-planner.

So I'm excited to talk about how, now, wearing your financial planner hat, you've actually looked to implement tax planning in your practice and systematize this. I know you have a lot of clients and a lot of teams. So us doing it is one thing, but how do we systematically put tax planning into an advisory practice is a whole other level of, I guess, complexity and opportunity. So, to kick off, I'd love if you could just share a little bit about your advisory firm as it exists today, just to give us a little bit of context overall.

What Debra's Practice Looks Like Today [05:14]

Debra: Sure. So we are part of Carson Wealth, which is one of the largest RIAs in the country, with $50 billion in management. I've been a partner of Carson Wealth for over ten years. Prior to that, I was with LPL for a long time, and I got my start actually with H.D. Vest. So I was with Carson for ten years, and then, in January of 2025, I made the decision to become wholly owned. So we are now Carson Wealth, Franklin Lakes, located in Franklin Lakes, which is the area that I grew up in. My office has been there for over 25 years. And in our office, we are managing $500 million, with about nine team members and about 120 core clients/families, is what I would say.

Michael: So 120 is your client base, and there are other clients amongst the nine team members, or that's the whole client base, $500 million of AUM? So you've got some sizable folks in there.

Debra: Yeah. So we are managing our clients, our families sort of as a team. So it is 120. Now, technically, it's 200, technically. But it's that old 80-20 Pareto rule where literally 90% of our revenue comes from these 100 or 110 families.

Michael: Okay. And so the other 80 or so are proverbial legacy clients that we took on at some point in the past when minimums and dollar amounts were lower, but you haven't transitioned or adjusted them, you're just keeping them on the book.

Debra: Yeah, that's correct. My junior team members are handling most of that.

Michael: Okay. Okay. So help us understand a little bit more just the composition of nine team members serving 200/120 clients. That feels like a pretty high-touch level of team, which makes sense given $500 million of AUM for 120 clients. There's some sizable client households here. But just help us understand a little bit more, how does that nine-person team structure work? What are the seats on that bus?

Debra: Yeah. So it is, right? It is a high team member-to-client ratio, is what I remind folks when I'm sitting in discovery meetings, and I basically tell them that you're not going to see a ratio like that anywhere outside of a family office. So we're really proud that we are servicing our clients well, and my guess is we'll get into that a little bit more. But what it is, and of course, it's evolved over the years, Michael, but right now I focus mostly on the vision of the firm, sort of technology, what direction we're going to head. I oversee the tax planning aspect of the firm, and I do the business development. So that's me going out and bringing in new clients to the firm, which is incredibly time-consuming, particularly since we're bringing in larger clients. So that's what I do. For example, two weeks ago, we closed $50 million, which does not happen every week. Yeah, I know. But the time involved out there is tremendous. And so that's what I do.

And then my husband works with me, and he joined the firm over ten years ago. And he handles the client service. So he's the one actually meeting with a lot of the clients and the investments and oversees operations. So that's what he does. And then we have two client service managers, and they're handling day-to-day requests. And one of them is also meeting with clients, some of those smaller clients. And then I have two planners. And I also have my daughter, who's in the firm, and she's the director of wealth strategies. And then I have two admins.

Michael: Okay. So help me understand just a little bit more of the distinction of roles. What are the differences between client service managers, planners, and admins? It sounds like there's two of each. I don't know if that's literally two pods of three people each, but what are those actual roles?

Debra: Yeah. So we're doing a fair amount in our office. So, yes, we're running the advisory practice, which is basically $500 million. But I also do a fair amount of writing and speaking. And so that work is generated out of the office. And then I'm also the chief tax strategist for Carson, and that work is also generated out of the office. I'm basically running three businesses, which I think you, of all people, could probably relate to that, Michael, okay? And so, anyway, some of the lines are blurred, and we keep busy.

So basically, the two planners, one of them does more of the core planning, is what I would tell you, and that's a lot of the eMoney. Yes, we have MoneyGuidePro, but a lot of that focus is sort of eMoney and building those plans, doing that data intake, that job that most people are pretty familiar with. And then my other planner is a more senior planner, and he has a tax background. And so he helps with the tax planning and the estate planning work and some of the larger clients, those more complex questions. So that's the division of labor between my two planners. Yes, they work together, they support each other, but there is sort of a loose division of labor there between the two of them.

And then my two client service folks, one of them is really focused a lot on operations and also, believe it or not, chasing down a lot of this AI [Artificial Intelligence] stuff and new technology. And my guess is you're probably...

Michael: So they're your person who likes to be tech savvy and play with new toys. So you let them go play with new AI toys and try things out and come back and tell you what's good.

Debra: Yes. Because of my total FOMO, so I'm reading all the time. And I just read about ChatGPT just for tax. I'm like, "I got to know about all this." And so she's the one...well, actually, this one went to my tax planner guy, so that might not be the perfect example. But when I'm reading about all this, "Oh, the best way to set up a prompt, four steps to set up a prompt." I'm like, "Hey, we need to learn about this. We need to get this right." So, believe it or not, what didn't exist probably two or three years ago now is actually a critical part of the firm leveraging technology. She's sort of the technology champ, is what I call it. And part of that is, of course, AI and seeing all those new developments. So she does then basic client service, "Hey, I need $5,000. I need basic trade." But also, she's helping to handle these operations and integrating technology.

And then the other client service manager has evolved essentially into an associate wealth advisor. And so he's sort of handling both jobs now, meeting with smaller clients and building into that. He's great with people, but also still handling some of that basic client service stuff as well. So that's where you see that division there, and that's evolving like all these jobs.

And then the two admins. And so we do a fair amount of marketing, social media, and my calendar is a nightmare, and helping to integrate the technology. And, look, we've got nine people down there. You're trying to make the trains run on time, and that can't all be on me. So that's with the two admins.

Michael: Okay. So, as I'm understanding, the core 120 clients would all still ultimately roll up to you. Those are "Debbie's clients." You've got this broad team to support you because of the admin support and the admin work, and the client service managers are handling the operations, and the planners are digging deep on the planning work. But you're still the point person for those larger relationships, and then you or one of your client service manager handles the 80 clients that have partially transitioned. Am I framing that well?

Debra: Actually, Rob, my husband, is the point person now on meeting with those big clients and sort of fielding those more complicated requests. So he's become the point person. It was me for many years, Michael.

Michael: Okay.

Debra: But now it is Rob.

Michael: Okay. Because that's what's freeing you up to do the biz dev, the writing/speaking, the chief tax strategist, that's actually remarkably hard to say, chief tax strategist for Carson, so this broader base of hats now that you wear.

Debra: That's right. And that's really evolved over just the last few years.

Debra's Shift From Leading Client Relationships To Taking On BizDev And Other Roles [14:16]

Michael: Okay. So, what drove that change or that shift?

Debra: Yeah. So, early on, Rob and I were sharing the meetings with the clients. And so we would sort of tag team, and he would take certain clients that would take others. And then as the tax planning role became more demanding, just overall, as the firm grew, as the client's needs grew, the services that we were providing expanded. That started taking more and more of my time. And what also started happening is I wasn't so close to the trading or the day-to-day work anymore. So then it became super stressful for me to go into these meetings, and it was like cramming for a final exam. And my guess is, at some point, you've had this in your career, years ago probably, but you probably remember that, right?

Michael: Absolutely. It's one of the reasons why I've been slightly skeptical about just how much some people say, the AI note takers, "Oh, if it completely automates all the follow-up and the meeting prep for the next meeting, you can just cruise out of one meeting and into the next meeting." I'm sure that's true from a technical record-keeping perspective, but it takes my brain a few minutes to get up to speed. These are real human beings that I need to be mentally and totally present for in walking into this meeting, and I can't Matrix-style download all of their detailed information into my brain. I got to load up my brain a little bit. And ironically, the more you delegate the tasks and the follow-up, whether it's to team or to tech, I find the more than you have to do to cram and prep to make sure, actually, just your brain is up to speed on all the things that are going on in this client's life before you walk into the room with them or turn on the camera with them.

Debra: Yeah. And it was the worst, to be honest. It was literally like cramming for a final exam three times a day. And they'd be like, "Oh, why do I own this fund versus that fund?" That's sort of a basic question, and I didn't know. So I had to cram for that. And why is there $50,000 of distribution? I don't know. And so it was super, super stressful in this sort of transition period. And now it just makes so much more sense because Rob and the folks supporting him, the client service managers, the planners…Rob's involved with these clients day in and day out. He's seeing the trades go out. He's the one signing off on a change in investment recommendations.

So then, when it's time for him to show up to the meeting...and we do surge meetings, Michael. So we're in meeting season twice a year, is how we describe it, and that's part of the whole service calendar concept. And so when he's walking into that year-end meeting, we're in surge meetings now, actually, he's familiar with what happened in May and what happened in August. So it's just a lot easier for him. It's a better client experience and not as stressful, certainly for him as it was for me. So this was a very nice evolution for us.

Michael: So then, are you completely out of client meetings because it transitioned to him? Are you still in with some role as well? How does that balance work now?

Debra: Yeah. So, believe it or not, I am completely out of client meetings, which, if you talk to me five or ten years ago, I would have told you that was nuts to be able to make that transition. Because there's definitely a Debbie cult, and people signed on for my personality and my expertise and my genius and my vision.

Michael: Particularly, for the depth of your expertise. I know we haven't gotten fully into the background yet, but I know you are a CPA and a lawyer. CPA, JD, there's a lot of really cool letters, degrees after your name, as it were. So that's a very deep expertise kind of brand to be able to transition to other team members.

Debra: Yeah. If it's nothing else, it's a testament to, first of all, how adaptable people can be under the right circumstances. Honestly, how amazingly competent my husband is, truly. The depth of the team and how strong the team is. And then I think it would go back to also the service calendar, is this sort of consistent outreach and communication and service delivery throughout the year, where people are seeing the value of sort of this model, as opposed to, "I have to have that semi-annual meeting with Debbie. Otherwise, I don't feel like I'm getting value, and I don't feel like I'm being serviced well." And I think we were able to move beyond, what I would tell you, a very archaic notion of how a financial advisor is supposed to run their firm, to be honest.

Michael: That's a really interesting framing to me that as you built out a client service calendar, that was something that could be more driven by Rob or, just broadly, by the team of Debbie's firm, not by Debie being in the meeting to talk the talk and say the things. If I'm interpreting, essentially, the shift to client service calendars helped to shift clients from being Debbie's clients to being clients of Debbie's firm that might have another advisor servicing them who isn't Debbie. Because, at that point, most of their value is coming from the service calendar of the firm. It's less Debbie-centric in the first place.

Debra: Yes. And so you can think of it in a few ways. First of all, I remember reading the Starbucks book, and they're talking about how, no matter where you show up to a Starbucks, foreign country, around the corner, it's the same experience. And there's something to be said for that. And so the service calendar does provide that sort of consistent experience and the visibility for the clients. And I think that was very powerful. And then, remember, the service calendar is a direct reflection of my vision for the firm. So it's not like I was necessarily pushing the clients out the door. I was like, "Hey, you're here, and we have the service calendar that Debbie has created, and this is how we're servicing you." So, yeah, it's worked very sort of comfortably, naturally, organically, yes.

Creating A Client Service Calendar To Provide Consistent, High-Value Service [20:47]

Michael: Very cool. So then, tell us more about the service calendar? What is this? How does this work in your firm?

Debra: So, yeah, if you will indulge me, so it really started ten years ago, Michael, believe it or not. And nobody was talking service calendar ten years ago.

Michael: No. Yes, that was not a thing then.

Debra: Right? So what happened is...and I'm telling you all my deepest, darkest secrets.

Michael: Appreciate that. We'll keep it quiet.

Debra: I hope nobody is overhearing what we're talking about.

Michael: Yeah, yeah, yeah. Mum's the word.

Debra: Yeah. So I've been writing articles for Horsesmouth, literally going back 28 years now. And I remember my first article for Horsesmouth is actually why you need an account minimum, believe it or not. So I started writing for Horsesmouth 28 years ago, and part of that was me being an attorney by training. I clerked for a federal judge. I was on law review. So I always loved writing. I always loved teaching. And I needed that outlet. I needed that collaboration and all of that that you're taught in law school and practicing.

So I'm doing this, and then people started reading my articles. And you start getting some calls from time to time. You know how this works because my guess is your version is something like that, right?

Michael: Yep.

Debra: So I get this call for my first keynote speech, and it's from Ohio National Insurance Company. And they've obviously been reading some of my articles, and they're like, "Hey, we want you to come, give a speech in San Antonio to our top producers. And they need to start thinking differently. They need to start thinking about providing advisory services, being more holistic. We've read your articles. We want you to do that." Now, Michael, I'm telling you this, I've never said this in public before, but I had never given a keynote speech in my life at that time, okay? So I had sat on a lot of panels at LPL. Every conference, they would always have me on panels and stuff like that. And I'd done some little...

Michael: This feels a little different when all the eyes are on you on the big stage.

Debra: Yeah. Right. And they're flying you out there, and they're paying you all this money. And you're supposed to be an expert. And they're like, "Are you really an expert?" I'm not so sure about that. I just write articles when my daughter's at the playground. And so, anyway, they're like, "Hey, we want you to do this keynote." And of course, I'm pretending that I do this all the time. So, anyway, that was over ten years ago.

And what happened at that time, as I was putting together this keynote, is I had lost a few pretty large clients during that 2015-2016 time. And they were clients that we serviced the heck out of, I went to his retirement party, all that. And it was really jarring to me. We lost three or four that year, and they were $4 million clients, $5 million clients. And it was very jarring. And they were going to what I call the custodians on the highway. They became do-it-yourselfers. And if you remember, going back around ten years, look, Vanguard's been around forever, right? But around ten years ago, if you go back, that's where this whole notion of robo-advisor and you can do it yourself. That's when a lot of it started gaining some traction, at least in my view. And people started becoming really aware of it.

So I'd lose some of these key clients. They're like, "Hey, I can do this without you. I can do this in the market. I don't need you." And so they leave me. And they leave me, obviously, for a cheaper alternative. And so I started thinking about it, and I'm like, "What happened here?" And it wasn't, "Oh, you didn't service them. You weren't proactive." It was nothing like that. And I'm like, "They resented paying fees. They did not think they were getting value."

And that's when I came up with the concept of evergreen service for evergreen fees. And the thinking was that, if your clients pay you 365 days a year, 12 months a year, 365 days a year, if your clients are paying you year-round, then you better be servicing the heck out of them year-round. So I came up with my first iteration of a service calendar for that keynote speech down in San Antonio. And I pretended that I was doing that, by the way.

Michael: Okay. Okay. So you presented the service calendar idea that you were going to start doing, and maybe weren't entirely clear that this actually wasn't already running in your firm, but it's totally where you were going, so we're just going to talk about it in the present tense.

Debra: Yeah. And I had it broken out to quarter. Each quarter, these are the services you should be providing. And so I presented it in that first keynote lecture and talked with them about how, if you were providing this level of service throughout the year, that it's high value and that you're not going to be botted out. Because back then, that was the precursor to AI, and it was, "Oh, you're going to get botted out." And I literally had these charts from Vanguard about three levels of service and needs. And one of them was the most basic, "Yes, it gets botted out, it's repetitive, blah, blah."

It's amazing, by the way, ten years ago, the same analysis applies today. I dug out that keynote, those slides. And so the most basic was repetitive, "Yeah, that gets botted out." But then, at the highest level, they had three levels. The highest level was creative, novel, problem-solving, and interdisciplinary. And I'm like, "That's where you are with this service calendar. That's where you are, providing tax planning services, and you're not going to get botted out. And then we're going to do this 12 months a year. We're going to show value, without a doubt," is what I would call it, copying from Omani Carson, "show value without a doubt, and this is going to keep you employed and help you get clients." So the service calendar concept started ten years ago. So I couldn't put it into practice immediately because I didn't have the team in place to do it.

Michael: I was going to say, paint the picture of just, I guess, where you were, where the firm was at this point.

Debra: Yeah. We're a third of the size we are now. So it's me and two junior guys and an admin, basically. So I've got the idea, but I don't have the team in place, nor do I have the process. So that's the other thing. If you have a service calendar that is four seasons and you're doing all these services year-round, you need process around that. And I didn't have process either. So I don't have team, and I don't have process. So basically, what happened then...but I'm committed to the idea because I know this is our way out. I know this is how I protect fees. I know this is how I close business. I know this is how I differentiate. I know this is how I retain. This is clear as day to me. So I know I have to do this, and I just got to figure out how.

Okay. So I start building my team as the practice grows, and I have an amazing paraplanner with me, and she's been with me almost seven years now. So if you go back and think about the timeline, then, it's 2015, 2016. I do this keynote. I lose these clients. I have this epiphany, essentially. And I'm like, "Service calendar." And that's 2016. Well, two years later, I have this paraplanner join me, and her name is Jen. She's still with me. She's amazing. And she's very methodical, very process-driven, just very methodical. And together, she and I start building out, one by one, the service calendar, where basically, every year since then, we have added additional services, refined, maybe some we take off or some then only get geared towards the A or B client and segmenting a little more thoughtfully. But basically, with her, over the last seven years, we methodically built this service calendar to where it is today.

Michael: So I'd love to hear more of what was on the service calendar originally? What was version 1.0? And then, what does it look like today?

Debra: So I guess, this is obviously testing my memory going back. There's been so many iterations. But early on, I'm thinking about that slide that I used. And early on, it was the basic stuff that we're talking about today, which, again, back then, you weren't really telegraphing it so much in a proactive, "Yes, you can count on this way." So it was like, "Oh, we do an estate planning review every year. Oh, we review your tax return every year. Oh, we review your insurance coverages every year. Oh, get us your long-term insurance policy. We review that every year." So it was stuff today that you're like, "Oh, that's sort of second nature, maybe." That stuff was what we were addressing.

But what was, again, sort of novel about it is we were assigning a quarter or a season to it. Now it's season. Back then, it was quarter, because quarters are too rigid. So that's why it's winter season, spring season, because things sort of flow a little bit. But back then, it was quarter. So it was like, "Oh, first quarter, we're going to review your tax return. We're going to review your estate plan. Oh, second quarter, we're going to review all of your insurance coverage. Oh, third quarter, we're going to update your plan every year without you asking."

And here was my other very novel idea, and I still have to beat the drum on this, is I do not want services attached to meetings, Michael. Okay. There's nothing that makes my blood pressure go higher than when I'm sitting with a team member and I'm like, "Oh, how are we providing this service?" And they're like, "Oh, well, when the client comes in, we're going to do that." My team knows, do not ever attach something to the meeting unless that meeting is happening literally in the next 48 hours, and you can 100% count on that meeting. Because, to me, that's a very antiquated concept of attaching services to when the client shows up. Because what we're seeing, particularly post-COVID, is clients don't want to show up. A lot of clients don't want to meet with you. They're busy. They're traveling the world. They're babysitting their grandkids. They're not in great health. They're remote.

And so one of the things that got me very upset, to be honest, is clients that weren't meeting with you, clients that weren't sort of holding your feet to the fire were essentially getting punished because that flurry of activity for the dog and pony show, is what I call the meetings, that flurry of activity in connection with the dog and pony show only happened when that client showed up to sort of get their pound of flesh and to hold you accountable.

Michael: So, if all of your service activity is tied to meetings, then, A, we end out in a world that a lot of us are higher-tier clients, get more meetings, and therefore, get more service because service is added to meetings. But you end out with a weird reverse effect, which is clients who might otherwise love us but just literally don't want as many meetings, because ironically, we're doing a great job, so they don't feel the need to meet, don't want to meet, and then, if they don't meet, they're not actually getting the service level anymore because we attached it to the meetings that they don't feel they need.

Debra: Yeah. And so, ironically and sadly, the clients that trust you the most end up getting hurt. And that really bothered me from an ethics standpoint, to be honest. So that's where, again, goes back to 365 days of service, evergreen service, evergreen fees, is we want you to have a consistent service experience that is not reactive. You don't need to call and say, "Hey, did you update my plan this year?" No, we handled that over the summer. That's on the service calendar. And we share that service calendar with you at the beginning of every season so that you see what we plan to do for you this season. And we are delivering these services whether you meet with us or not. You are getting these services. And in a way, then, it tacitly, I don't want to say, discourages those meetings, but it sends a message to clients that you don't need to haul your butt out here and sit us down for a meeting to get the value that you deserve.

What Debra Puts On Her Client Service Calendar [32:49]

Michael: Okay. So I'd love to hear more about, I guess, literally, what's on the service calendar and how it evolved. At the beginning, you said it was, "We do an estate review for you in one season. We do a tax review for you in another season. We do insurance coverage review in another season." It sounds like that's not where it is now, or not all of this now. So, how did it evolve as you started doing this?

Debra: Yeah. So, early on, then, it was some of those more basic deliverables, is what I would say. Although, again, back then, it was revolutionary to be...

Michael: You got to walk before you run, right? Anything in place is amazing when you don't have a structure. Then, when you get a structure, you start adapting, because that's what we tend to do.

Debra: Right. So, okay. So then we start with some of those sort of, again, today would be considered more basic services. Also, remember, we have the technology today to help us deliver this stuff more efficiently. So, back then, when I said we were reviewing tax returns, I'm doing that manually. So again, everything was a lot more complicated in that sense. And so, okay. So now we start building on the service calendar. So what would happen then is, every season, which loosely lines to the quarter, we would have two services or three services for that season. And so, back then, so I'm saying now the late 2019, 2020, so around there, so it was the estate planning, the tax return review, the different insurance reviews. Then, also part of the service calendar was reviewing your retirement plan contributions and making sure those were set up, updating your financial plan annually, absent a meeting. And then part of this was also having two review meetings a year.

So one of the things that we did with the service calendar is most of your A, A-plus clients get four meetings a year, sort of that traditional cadence, quarterly meetings. And they feel like if they don't have the quarterly meeting, they're not getting their value. "Oh, we get our quarterly meeting." What we did is we went down to two meetings a year, even for the A, A-plus, went down to two meetings a year. And we call this like when the kids are young, it's called remove and replace, where you're like, "Oh, why don't you give me mommy's diamond ring? And I'm going to give you this really cool stuffed animal." So we're like, "Okay, we're going to go from four to two meetings a year," which, by the way, back then was revolutionary because that's the only way you saw your value, if you're looking at it through the client's eyes. So this was very risky for us. So we're like, "We're going from four to two meetings a year. But instead, now, we're providing these services throughout the year."

So we're going to have all this touch throughout the year and all these high-value-add services that are custom to the client throughout the year. So you're talking to us throughout the year, but you're going to have your two sort of review meetings. Your dog and pony shows, you're going to get those twice a year. And those are going to be in surge meeting sessions. And the surge meetings season starts right after tax season, because during tax season, we're very busy supporting tax planning, supporting CPAs who are totally overwhelmed, all that. So it starts right after tax season, and it goes for a month and a half, and then year-end. And so, right now, we're in the middle of the year-end part of it. So now all the clients went from four to two. And if you were getting two or three meetings a year, you were going down to one or two meetings a year.

But in its place...so you're like, "Oh, I never get to talk to Debbie's team. They're not doing anything for me." Well, in its place, we have this service calendar that gets sent to you every quarter, and there is constant outreach on all these other things that, by the way, are far more important to you than me reporting back to you, how much Amazon went up last week, when you get to see that on your daily portal anyway. So that's the swap. And I will tell you, we have not lost one client or honestly registered one complaint with someone who is like, "Hey, I used to see you four times a year, and now I only see you twice a year."

Michael: So I have so many questions. My brain's overloading. So, what's on the service calendar now? What populates into the seasons at this point?

Debra: Okay. Yes. So I had to pull out the service calendar because there's six. There's 20 or 25 things on it, so I had to pull it out. So, okay. So the winter season, which it says literally winter season/beginning of year planning areas for review, that's literally what it says. So that's at the top. And that's prepare the CPA tax summary letter for prior year transactions. You know what that is, right?

Michael: Yes. But can you explain for folks who have not created one of those? We used to do a version of this in my prior firm. But what does that look like for you guys?

Debra: Yeah. So the year before, first of all, your clients forget what they did. They forget that they authorized a Roth conversion in April of 2025 when the market was down 20%. And you were proactive, and so you did a Roth conversion for them. They forgot about that. They forgot that they did a QCD [Qualified Charitable Distribution]. They forgot that they took money out of 529 or that they paid long-term care premiums that are partially deductible.

So, anyway, we do this tax summary letter for prior year transactions for our clients. It's actually very time-consuming because it's like a little treasure hunt. Obviously, the software is not all integrated to deliver this type of summary. So, anyway, it's a lot of duct tape, cutting and pasting. So we put that together. So that's one thing we do. And the clients really appreciate it.

And then, also, in the winter season, we create the budget for the year, the cash flow, company benefit plans we're also reviewing, so where that money is coming from, what that budget, the cash flow, how much you need every month from your retirement account, all of that. And then, in connection with that, we create the distribution plan. So the distribution plan is not, "Oh, you take $5,000 a month. We're just going to take that out of your taxable account because, today, that's really great. Lower taxes for you because you got preferenced capital gains treatment, blah, blah, blah." We know better than that. We know we don't want to be drawing down those taxable accounts while that huge traditional IRA is building in the background, and we probably should be drawing that down, or whatever.

So we do a distribution plan in the beginning of the year where we address RMDs [Required Minimum Distributions], we address QCDs, because we know QCDs should be taken before the RMD to be most effective, and we coordinate their tax-efficient withdrawals and also integrate a preliminary Roth conversion recommendation, which needs to be really part of all of that. And so, yeah, that's a big thing we do in the first quarter, the first season. Then also setting up retirement plan contributions and then having an annual tax planning meeting for clients who desire that.

Michael: So, just how does the production work of all of this stuff get done across 100-plus clients in the span of a quarter before we just get to the next quarter's worth of stuff, which we'll probably talk about in a moment?

Debra: Yeah, that's what took so long to go from theory to application. So the CPA tax summary letter, Holistiplan has a template version of that. And so that's a helpful start. And Jared, who is the associate wealth advisor that I mentioned, client service manager/associate wealth advisor, he handles the CPA tax summary letter. He's done it for years. We have an entire checklist. So everything has a process. So one of the expressions I have, if we're going to do it more than once, you need a procedure. You need a checklist if we're going to do it more than once. So, for example, when I go out of town on a conference, we have a checklist for that. When I take vacation, we have a checklist for that. Everything has a checklist if we're doing it more than once.

So we have an entire checklist around how to put together the tax summary letter, which transactions are going to be included, where we go to pull that transaction to, included in the letter. So Jared handles that, and he's done it for years. It's a headache, Michael. He literally goes out of pocket for a week or two to put these together.

Michael: Okay. Look, when you've got multimillion-dollar clients who are paying you tens of thousands of dollars a year, yeah, I got a team member who goes out of pocket for two weeks to produce the really valuable thing they like. Cool. That's why they pay us for service. That, to me, is that...I hear that. And I know, just my gut response, well, yeah, providing high-touch service to high-value clients, someone's got to do the work. That's just part of the deal.

Debra: Yeah. And that's literally what I say, is they'll be, "Well, do we really need to do this for the client that has less than $2 million with us?" There's an ongoing negotiation on all this stuff, okay? Always. Always. And I'm like, "Yeah, that guy paid us $25,000 last year. That guy pays us $2,000 a month. He's getting a tax prep letter." So there's constant negotiation.

Michael: It's powerful when you put it that way. He's paying us $2,000 a month, and we've got 100 people like that. Do you think someone can take two weeks to put this high-value thing together for people who are each paying us $2,000 a month?

Debra: Yeah. Yeah, 2000-plus, right? Yeah, exactly. So Jared does that. Again, everything needs a process. You cannot do the service calendar without process behind every single one of these icons, is what we call it. I'm looking at our service calendar. And so, for the winter season, there's six things listed, and they each have a little mini graphic pop art thing. So we call it the icon. And you need a process behind every single one of these things. Otherwise, you're not going to be able to deliver them on time and thoughtfully. To your point before, "Hey, this sounds like a lot." And that's, again, going back, why we have nine team members for basically 110 core families, is because we are doing this.

Michael: I guess the one question I would have, Debbie, just for folks maybe who are listening to follow along, are you comfortable to share a copy of what this looks like that we could post to the show notes just for people who want to look along for the visual?

Debra: Yeah. Sure.

Michael: Awesome. So we'll have a copy. So, for folks who are listening, this is episode 470. So if you go to kitces.com/470 and scroll down to the show notes section, we'll have Debbie's client service calendar posted as a link there so you can look and follow along as we talk through here.

Taking A Flexible Approach Towards Distribution Planning For Clients [43:41]

Debra: So then the next part of these icons is this whole, really, distribution planning for the year, income/expenses, what we need each month, how we're going to get that. And then that really needs to tie into Roth conversion recommendations. Because if we've got a large IRA that we're trying to draw down a little bit, and we're like, "Oh, well, we're going to take $15,000 a month from the traditional IRA, then maybe we don't do as much of a Roth conversion because we're drawing down the traditional IRA by other means." So, in my view, this really needs to be coordinated and not isolated.

And so what happens is this whole notion of people waiting until the end of the year to do tax planning, again, is, to me, a total misnomer. The market is up two-thirds of the time in the last quarter. It has an upward bias. And this year is a perfect year as an example, is we did Roth conversions for our clients in April when the market was down 20%. Why would you wait till now when the market is up 20% to be doing those Roth conversions? And I understand the arguments to do that, "Oh, you have more visibility into what their income/expenses are for the year." I get that. I understand that. But during the year, there are so many opportunities that can be presented to do Roth conversion work that I really rail against the rigidity of putting tax planning into Q4. I think it's the lazy man's way to approach it, to be honest.

Michael: I've just got to ask, on that vein, though, when you're running this kind of quarterly structure, how do you still be, I guess, flexible and adaptive to something like Roth conversion planning, is a great example, if you want to do it more opportunistically? I hear you on the challenge of doing it as a Q4 exercise, but I feel like I can pull it to Q1, but then I also risk pigeonholing myself into Q1. How do you stay flexible through the year when you're still trying to manage to this structured calendar through the year?

Debra: Yeah. And I think you say it best, Michael, is the flexibility. So we put this together in really this...it takes till about February, to be honest. And I'm just hoping and praying the whole time that the market doesn't tank during that time, and we haven't put together our preliminary Roth conversion recommendation. So I'm on pins and needles, and I'm like, "When's that going to be done? When's that going to be done?" Because I knew the market was going to pull back this year. I knew it. And so, thankfully, it didn't happen till April.

So what happens then is we put together our preliminary distribution plan for the year, because that's really what it is, "I need $5,000 a month to live off of, good. I have RMDs coming. Okay. How does that sort of factor in here? Here's our Roth conversion recommendation." And even QCD, right? So just really putting together that very basic distribution plan.

Okay. So now we sort of go to the client with that in, let's say, February, and we're like, "Okay, here's our idea for the year. You need $5,000 a month. We're going to take $2,000 from your taxable account. We're going to take $3,000 from your traditional IRA. And you're not doing QCDs this year because you're not interested. And here is our high-level recommendation, is we think you should be doing about $100,000 Roth conversion this year." And the client's like, "Great. Got it." Okay, we're setting up your distributions. All is good.

And then what happens is around April 2nd, Trump announced his tariff idea, and the market just completely tanks. And so my team is prepared. We hop on it, we reach out to all the clients that had gotten those initial recommendations, and we have a whole spreadsheet that manages this process. I am not aware of great software that manages this yet. And we do the outreach that week to these clients. And we're all hands on deck. Okay. We have a list. We're like, "Okay, you're reaching out to these 15 people. Okay, you reach out to those other 20." So it's all hands on deck. We reach out. We're like, "Hey, early in the year, we made the recommendation to you for $100 [thousand dollar Roth conversion]. Market's down 20%. Maybe it was only down 15 [percent] because sometimes you're early a little bit on these things. We think this is a good time."

So now here's what happens, is you get different responses. Clients that have been with us a while, they've seen that we've done a very good job of timing this. So, for example, in 2022, we did conversions in June, and we did them in October. October is when the market hit its bear. We did conversions in January of 2023 of technology companies. If you remember, Michael, everybody was writing off technology in January of 2023. And we said, "No, tech is going to come back." So, who does Roth conversions in January, breaks every rule? Well, we did. These clients who have been with us for a while, their Roth accounts now are huge, with all of those gains from these conversions. So, if we're calling one of them, they're like, "Hell, yeah. Do what you want to do." Because they see this growth in their accounts, and we constantly remind them of it. Okay. That alone pays my fee every year, that work.

All right. Clients that are newer or have things in motion, "Hey, I'm selling a partnership. I'm not really sure this year, the tax burden might be so high," so those folks might waffle, or newer folks waffle because they just don't know completely how to follow our direction sometimes. Okay. And so...

Michael: Oh, you have those clients too?

Debra: Yeah, exactly. Yeah. They don't realize that we're literally right 95% of the time, okay. And so they're like, "Wow, I don't know." And I have a lot of these self-directed people come to me, Michael. We didn't get into your client base. But we have a lot of these retired engineers, retired doctors, smartest guy in the room, and they're coming to us for tax planning because it's the one thing that they couldn't figure out how to do on their own. And they're not happy about that because they swore they'd never pay an advisor. They're the smartest guy in the room. They bought Microsoft and NVIDIA. What else do they need to do? And now they hit the distribution phase, and they're just like, "I've read all these websites. I've read this, I've read that. I understand I need to do this, but I don't understand how." And I'm like, "Yeah, I do this all day, every day. We understand how." And so they're sort of kicking and screaming on their way to the altar.

So then some folks need a little bit of convincing when they're newer. So they'll be like, "Okay, I understand what you're saying, but I'm not really sure." And so they'll do half. They'll do a quarter. And we're like, "Okay, fine. We'll do $30,000 now. We'll circle back later in the year when other opportunities arise or at the end of the year when we have no choice." And they're like, "Okay." So there's a little bit of compromise there. And then other people, it's legit, "Hey, I'm selling my business. I'm not really sure what tax is this year. Can we wait?" And we're like, "Yeah, totally get that." And so that's what happens.

If there's a second opportunity during the year, we will circle back. And then now we are circled back. I call it last call at the saloon. We're like, "Hey, we reached out to you in April. You gave us a pass," or, "You only did 30 of the hundred. Now we're back. Last chance. Where are you on this thing?" So, anyway, that's the distribution planning, and that's sort of the cadence. That's Jen's area, my paraplanner who's very process-oriented. She literally has a 13-column spreadsheet where we track all of this. And, yeah, that's how that part happens.

What Client Meetings Look Like Under A Client Service Calendar Framework [50:48]

Michael: So then, take us through what comes on the service calendar in the other seasons. So I get, Q1 very much kicks off in the tax theme, tax summary letter, spending for the year, distribution plan for the year, tax planning meeting, retirement plan contributions, a lot of those elements. So, what comes in the spring season?

Debra: Yeah. And also reminding of QCD before RMD. Yes, yes. Good. Spring season. So this is our semi-annual investment deep dive, is what we call that, which is going into their investments and doing exactly that, a deep dive, a review. So that happens in spring. Then we have our...

Michael: And this is also when you have your first surge meeting, in the spring as well.

Debra: And that's the next thing I was going to say, is, yep, then we have our mid-year review with the client. So that's our surge meeting, happens right after tax season. We update financial plans for all clients without asking, without it being connected to a meeting, and we send them a one-page financial plan through eMoney and a video with that explaining the plan. So that also happens during the spring season.

Michael: Wait, how does the video thing work? What are you doing?

Debra: Yeah. So we wanted to sort of make this come to life. So, first, we did the one-page update, which we were thrilled with. And then we'd have a cover email. And my concern is that clients don't read some of this. They're overwhelmed. And I like to meet clients where they are. So then I was like, "Okay, let's do a video." And clients like videos. I don't, Michael, by the way. I like transcripts. I read a lot faster than I can listen.

Michael: Okay. So you'd rather read it than watch it, but a lot of your clients would rather watch it than read it.

Debra: Yeah, they want that human connection. They're retired. Most of our clients are retired. They have a ton of time. So like, "Oh, let me click on the video. Fine." So we do a three- or four-minute video sort of discussing the plan with them. So that goes out.

Michael: So you're recording one video for each client to walk them through?

Debra: Yep. And it's through BombBomb, actually. And with compliance, they don't have to approve it in advance. So that works out well. And we send that out. Yeah. And look, and we say, "Hey, if you want a meeting about this, if you want to go deeper, let us know. We're happy to have that meeting." By the way, just to address what probably every listener is wondering right now, is they're like, "Oh, my gosh, she's doing all these things." We're going to be performing all these services for every single client. It's amazing how there's a self-selection process, where clients aren't tapping you for every single thing. They tap you for what's important to them. So there's high ROI on it, if that makes sense.

Michael: But if this is the service calendar, do you have to do all the things for each client? How does the opt-in/opt-out part of this work if the whole point is it's a standard service calendar that "everyone" gets?

Debra: Yes, you ask excellent questions, Michael. So what happens is we send out announcements throughout the year, is what we call them. And they're single-purpose. So I have a weekly newsletter. It goes out on Monday, covers 50 things, whatever. This is different. This is single-purpose, with a very clear subject, and it's one thing. It's Medicare open enrollment. It's, "We will review your benefit plan." It's, "Time to submit your income and expenses to us so we can review your budget in January." And so we send these announcements, and we send 30 to 40 a year. So literally averages about three a month on different aspects of the service calendar that require the client's engagement, essentially.

So, for example, we're talking about spring. The next thing I was going to mention, real quick, is the spring review meetings, which we talked about, the surge meetings, and then the estate plan review. So this is a great example. They'll get an announcement at the "beginning of the season." So that'll be April or May. I'll be like, "Hey, that time of year is here, where we review your estate plan. Let us know of any updates, any questions, anything you want to talk about." And then we'll provide some information of things that they should be thinking about. "Oh, remember, you want estate plans to be no more than five years old, ideally." We'll provide them some information, some articles I've written, maybe, whatever. And so we send that out.

So then the first thing you worry about when you've never done this, you're like, "Oh, my gosh, she has 110 core clients. I bet 60 of them reply. And now they have all this work on estate plans." It doesn't work like that. We'll have five reply. And then some don't reply right away. Some get this, but then two months later, they'll follow up and be like, "Hey, you sent this to me, but I was in Europe," or, "I had some things I had to work on. So, can we have that conversation?" So it's not nearly as overwhelming as it would appear to be on the surface.

Michael: So you're not automatically queuing up the full boatload of work for all the items on the client service calendar. For some of these, there's something the client has to do first to trigger and begin the process, which means, if the clients are not so engaged or just aren't that into the thing, they won't do the first step part that they have to do, which means now you are not obligated to do the rest because they didn't do the step one for you to do the rest. And presumably, it's not that important for them that you do it, or they would have done their parts. They're kind of self-selecting at that point.

Debra: Yes. Right. So some things are happening to them no matter what. We're just doing it. But then other things, going back to winter, is setting up and reviewing retirement plan contributions. Well, I can't do that unless you get me your benefits booklet. I can't make recommendations unless I know what our options are, right?

Michael: Right.

Debra: So we'll send out an announcement and say, "Hey, it's that time of year again. We're happy to help you with this. Get us your benefit booklet. We'll walk you through. Well, if you don't get us your benefit booklet, I can't make those recommendations to you."

Michael: Interesting. So a piece of the service calendar is systematic work, and a piece of the service calendar is systematic offers to do work, that they have to engage to actually get said work done. And in practice, not all engage, a quarter or third, maybe all that engage with a lot of things. Everyone gives you credit for asking, but not everybody actually needs you to do the work.

Debra: And yeah, that's what I love, is it's a huge goodwill generator.

Michael: So I guess, now, just for the things we've talked about, what are the automatic ones and what are the optional or the announcement, must engage ones? Can you delineate those for us now that we know there's a distinction between them?

Debra: Sure. So in the winter season, the CPA summary letter, you're getting that. Review income and expenses for the year, analyze company benefit plans, and setting up retirement plan contributions. You've got to engage. I don't know what your income and expenses are for the year. Then preliminary Roth conversions, you're getting those. You're getting that. So some of the things, Michael, I feel are so important that even if you are completely checked out on me, we're banging down your door. So the preliminary Roth conversion, if you've got a $4 million traditional IRA, but you're checked out, you're still getting a Roth conversion recommendation from us. And we will literally follow up two or three times with you on it, because I'm just like, "No." "Well, we reached out to them." I'm like, "You need to chase them down. This is important."

So the Roth conversion thing, you're getting, no matter what. The CPA tax summary letter, you're getting no matter what. When I say Roth conversion, I'm referring to, also, the distribution plan, that whole thing. And then option is the tax planning meeting/family retreat/charitable giving review. That is optionality. You can't hold a meeting if no one shows up. All right, so that's winter.

Spring, the semi-annual investment deep dive, we're doing that, no matter what. The mid-year review potential tax strategies, we're doing that, no matter what. Update financial plans, we're doing that, no matter what. Spring review meeting. So if you don't show up for our two meetings that we call you to, you get a written review. So you're getting something, but if you're not showing up, then you're getting a written review. So I'm not sure how you would count that one.

Michael: Well, that was actually going to be one of my questions, because you said there's an investment review, which, it sounds like, you're trying to do all these things, not necessarily tied to meetings. So if there is an investment, the planning review happens outside of a meeting because it's a video. The investment review, it sounds like, is written. So then, what do you do in the meeting? Will you actually talk about meeting at this point? Since you were very diligent to dissociate all the service work from the meetings.

Debra: Well, that's why a lot of folks aren't feeling so compelled to come meet with us. It's because we're bombarding them all year. But all joking aside, some of this, we'll sort of time it together. So it'd be, "Oh, Jim's coming in in a week, and we're supposed to be doing the semi-annual investment deep dive." So we'll do that, and we'll present that at the meeting because Jim's coming in literally in a week. So some of that will have timing.

Michael: Because you said earlier, if the meeting is actually really close, truly close coming, we can tie the service to the meeting. Let's just not drag out the service waiting for a meeting.

Debra: Right, exactly. But then what happens, Michael, is most of our clients are $3 million to $6 million, most of them, and some are larger. We did the math before, 110 clients, $500 million. So you do that math. So if you show up, and let's say we're doing all these services, and most of them are "mandatory," and then maybe a third of them are "optional." And this is all happening throughout the year. So then you're just like, "Debbie, what are you doing in the meeting?" Well, remember, these people who are showing up basically have $4 million or $5 million. They have lives. They have a lot of stuff going on. They have kids. They have grandkids.

So there's always something to talk about in the meeting. Maybe it's a matter of following up on some of the work that we did do earlier in the year, and they're like, "Hey, you sent me that thing in February. Can we just talk about that now? Because I didn't really understand, or I have more questions." And also, these people, there's a lot of, then, legacy planning, children, grandchildren, stuff going on. So there's never a meeting that Rob walks out where he's like, "Yeah, we had nothing to talk about." When someone has $5 million, they're always cooking up something. So that's our experience. Oh, and then the other thing is all these tax law changes.

Michael: I've heard about those. I read something on the internet about those.

Debra: Yeah. It's called the Kitces and Taylor Full Employment Act.

Michael: Seriously.

Debra: Yeah. So one of the things they're doing in these surge meetings is they're going in prepared to talk about OBBBA [One Big Beautiful Bill Act], and we have an entire chart, and we walk through different aspects of it that could benefit or affect the client, what that looks like for them, and a lot of questions on that, too. So, yeah, we have new tax legislation almost every single year. So that alone is a portion of the meeting.

Conducting Tax, Insurance, and Estate Planning Analyses For Clients [1:02:20]

Michael: So, okay. So now keep us moving through the seasons. So, what comes in fall season now?

Debra: Oh, we got to go to summer.

Michael: Oh, sorry, summer. Yeah.

Debra: Yeah. Okay.

Michael: However those things sequence. Sure, let's do summer first. Okay.

Debra: You only have three seasons in your world? Okay. So summer is tax return review and analysis. So you notice that's showing up for the first time in summer because everybody goes on extension. Right. So that, you're getting, no matter what. Okay. So that is through Holistiplan, obviously, and we have a whole process around that. So, again, originally, okay, tax report. Five years ago, when Holistiplan came out, we were like, "Oh, my gosh, this is better than being able to create fire." But then we realized, "Hey, some of the clients might not be reading this tax report." So now we have a cover email that goes into some detail about what is a Medicare surcharge, and stuff that they don't understand, and how OBBBA might be affecting their tax return. So there's the tax report, and then there's a cover email that is customized for the client that addresses if they're itemizing standard deduction, whatever is going on in their world on their tax return. So everybody gets that. So that's summer.

Then, also summer, we revisit the Roth conversion analysis, sort of a mid-year thing, "Hey, checking in." We do insurance review. If you notice, I hadn't mentioned insurance yet. So you're getting that. And then we do create, and we've had some trouble with this, Michael, full disclosure, the goal review and report card. So I'm absolutely obsessed with quantifying how people are doing with their goals. And you've written about this and talked to people about this. As you come in, you're like, "Oh, Monte Carlo, you have a 90% chance of success." I don't even know what that really means. What does that mean?

And so what I think is more meaningful for people is to say, "Hey, you had these ten important goals," or honestly, more like 30 or 40 in these five or six key areas of your life, if you really break it down, and we have red, yellow, green, where we score it on a scale of one to ten, how we're doing. And then it's very visible. And then we can say, "Okay, here are the areas that you're successful in. Congratulations. You have a great financial advisor." And we're wonderful. "Oh, and here are the areas we need to work on," and that keeps us employed.

So what happened is we tried to do this, and we couldn't get it through compliance, to be honest. And so we've been talking with eMoney, and they actually keep promising that they're going to come out with some version of this. And we literally talk to them every month or every other month, "Hey, where is this thing?" So, anyway, that is something that's on here as aspirational, because it was actually supposed to come out this summer, and it didn't. And so it's on the service calendar, we plugged it in there, and we're hoping that it comes out soon. And we could start baking that in.

Michael: Because you need a systematized, now ideally, tech-enabled way to keep it on track and efficient when you're doing this across all the clients.

Debra: Yeah. And I want visibility for the clients. I want them to know how they're doing towards their goals, other than, "Oh, you have an 85% probability of success."

Michael: What else is in the summer season? Well, sorry, I guess, quick note, I'm assuming...well, I guess you can tell me, what's optional? What's automatic in this summer season of activity?

Debra: Yeah. So tax return review and analysis is automatic. Goal review is aspirational. I just created a new category for us.

Michael: Oh, yep, yep. I love it.

Debra: Insurance review is a mix of both because there's Medicare, life, long-term care, and P&C [Property and Casualty]. So some of them, you have to essentially opt in. You got to get us your P&C policy, right? And then some of them, we are reviewing on our own, like long-term care or life. We're giving you an update on our own.

Michael: Okay. Because you've presumably got the policies already. They don't change that often. We can review whether it's still appropriate, but we don't necessarily have a new policy collection the way that some people switch P&C much more regularly.

Debra: That's right. That's right. And then revisit the Roth conversion analysis. So, yeah, that's a checkpoint. And then one of the things I instituted, either a year or two ago, because I became totally paranoid about it, so it's a security review. And so, with AI being able to copy voices, and then the custodians, they don't want to accept POAs [Powers of Attorney]. And I think this is very, not really advertised. So your clients, they think they're doing their job. They go to their estate planning attorney, they get this fancy POA, and the custodians are like, "No, we have our own version here. We also have this trusted contact form over here, and you need to sign our stuff, not bring your own stuff." And so we ran into this.

So between cybersecurity issues, between AI being able to duplicate our clients' voices, and then between the custodians that are like, "No, no thanks. We don't like your POA. We got this own form over here," which, of course, by the time you realize that, it's too late, right?

Michael: Right, right, right. Yeah, yeah. "Here's my POA. My client's disabled." "Oh, we don't want this. We want a separate signed one." Well, they can't sign forms now. Did you not hear the POA part?

Debra: Right, 100%. And so it's a little bit disturbing to me. So we have, over the summer, a whole security review where we reach out to our clients and try to update those forms and get the trusted contact form signed and on file with the custodians and the custodian versions of forms that they want, all of that. So that's the security review. Okay. So that's us reaching out and forcing that down our clients' throats. That's the summer season.

All right. Heading into fall/year-end, so that is the final tax return review and analysis, because a lot come in in October, as we know. So that's sort of finishing that up. Then, end-of-year tax planning opportunities. Again, tax planning is a year-round activity. We're doing this year-round. But at the end of the year, we are in a calendar year, we have to sort of finish up whatever has not been finished up. And so that's any leftover capital gain harvesting, tax loss trading, funding the retirement account. Whatever is left over, we're doing that. We do our year-end review meetings. So that's the surge meeting twice a year. So we do a year-end review. Then the final Roth conversion for anything that's left over that you didn't follow up with us on or you didn't complete according to our recommendation.

And then, Michael, this is huge, is our year-end review. We call it wins and wows. Another total headache, although we are figuring out a way we think to "automate" this and simplify this. So we do amazing work for our clients throughout the year. My husband's gone to the Hamptons to help do a home inspection for a widowed client. We're doing all kinds of stuff, just like you are in your practice. And they forget, not in a bad way, but they forget. They're distracted, whatever. So you're paying us $20,000, $30,000, $40,000-plus a year. At the end of the year, you get wins and wows. And it's basically a summary and compilation of the amazing work we did for you all year, how we supported you on your journey, how we helped your family, how that Roth conversion made you $70,000 in tax-free growth already in that Roth IRA because we did it in April. And so we do wins and wows at the end of the year. It, again, is a total headache because we got to go to five different places to pull that information. But again, someone's paying us $40,000 a year. We want them to continue paying us $40,000 a year. They need to see what we've done.

Michael: It feels like something that an AI tool could help with, just in the word where the AI tools are getting really good at crawling everything in our CRM system. Crawl everything in my CRM system and help me create a summary of all the things that I did for my client for the year as a summary report for any AI tools or power users that are listening and want to share that with some of the companies.

Debra: Yeah. Yeah. There's a real opportunity there.

Michael: So, anything else in the fall season?

Debra: That's not enough, Michael?

Michael: Just check in.

Debra: No, that's it, Michael. That's it.

Michael: So there are a few things that strike me, just hearing this all the way through. So on the one hand, this really helps to connect back to where we started, 120 clients, nine team, which is it's a higher staffing-to-client ratio than a lot of firms. But your typical clients, $3 million to $6 million and paying tens of thousands of dollars a year in fees. So, from a revenue perspective, that actually sounds like a very, very normal level of staffing for the amount of revenue and the things that need to get done. The distinction is just, I feel like, for a lot of us, we have a large number of clients, a moderate number of staff, and we're trying to manage and minimize how much tasky work we have to do to keep the practice efficient. And you seem to have gone a very different direction, which is, "No, these are high-value clients. They pay us a lot of money. We're going to come up with a thing to do for them that's awesome, and we're going to do it. And we have the staff to do it, and it takes time, and that's what clients pay us for."

And then, later, you figure out how to refine or automate it. Because it does sound like you, as you know, you've created checklists, process, the technology gets better. You're pushing on eMoney to help with the one-page plan. We'll give the AI tools a shout-out to solve your year-end review wins and wows. The tech makes it better over time, which I'm guessing is how you've added so much to the service calendar now compared to ten years ago. But just correct me if I'm wrong, what I'm hearing, but the approach is first we just find a thing that the client would like and find valuable, and we do it even if it's messy and manual because they pay us a lot of money, and we just staff appropriately. And then, over time, we figure out how to get more efficient with it. And when it gets efficient enough, then we go find another thing to add. Because we're saving enough time, we can do it, and they're high-value clients, so they're worth it. Is that a fair characterization of the evolution for this?

Debra: Exactly.

Michael: So, what else has changed or evolved over time with this? Because you're ten years into these.

Debra: So we have added more, and that's consistent with all the studies to protect our fees. We're all providing more services.

Michael: It's why the whole fee compression thing just continuously turns out to be a myth. We don't compress our fees as we get more efficient. We do more things for clients with the time that we saved because we got efficient. And then we keep charging the fees we were charging because we keep doing more for clients in the process of getting efficient.

Debra: Yeah, 100%, absolutely. And so what's really changed is, I think, trying to be dynamic with this. So we're constantly reviewing this and saying, "Hey, we're offering this, but nobody's really interested." There's not high value, not high interest in it. So then maybe we drop that, or we de-emphasize that. And then, also, just being receptive to our clients and adding things. So, for example, the family retreat, that was not on there a year ago, but that's on there now. So I would tell you just being flexible with this.

Debra: And I see this because I teach on the service calendar. I talk about it very openly with Holistiplan at Carson. And the first response is, "Oh, my gosh, how am I supposed to get from here to there?" And that's one of the reasons where I start saying, "Hey, this started ten years ago, and it didn't look like this ten years ago."

Michael: Yeah. Don't look at where I am. Look at where I started.

Debra: Right. And what you do is I say, "Look, you're already doing some of this stuff." So now it's just a matter of documenting it, right? Because people are doing it. So just document it, share it, be transparent with your clients because they want to know what to expect.

Debra's Two Secrets For Closing New Client Business [1:14:26]

Debra: If you said to me, "Debbie, what are the two most important pieces that you bring into a discovery meeting that help you to close?" It's my service calendar, and it's one other piece that we haven't talked about.

But this is that powerful when I walk in because there is this natural skepticism that prospects have of, "Hey, what are you going to do for me? I'm paying you all these fees," and all the stuff they're reading in "The New York Times" about firing your financial advisor, whatever. When you walk in with a two- or three-page, because the first page, it's on one page, but then the descriptions are on page two and three, when you walk in with a very thoughtful, laid out, proactive plan about how you're going to protect this prospect and their family, we win.

So, anyway, I think, going back here, this is a living, breathing document. And you've got to be sort of iterating, adding security review, adding family retreat, maybe dropping things that aren't so important. Once we become more efficient at something, maybe then the other aspect of the service calendar is the segmentation of it. So that's the other thing, Michael, is you talk about...I'm lucky I have 110 core families. Most people have 300, 400, 500, even more. So they're like, "How am I supposed to do this?" This is where segmentation becomes really important, and that's something that we look at a lot in connection with the services, is we'll say, "Okay, CPA tax summary letter. This takes 45 minutes to do, or 20 minutes to do. Who needs to get this? A, B, C, D. What does that look like?"

And so what it does is it forces you to think differently about your segmentation, because traditionally, your segmentation was really just about your frequency of meetings with clients. That's really what it is. That's an A client we meet four times a year. That's a C client we meet once a year. Now segmentation is this is an A client, they get 13 services a year, this is a B client, they get 9 services a year, and so on.

Michael: So, what didn't work on the client service calendar? What's come off the list or de-emphasized in the end because you did the thing, and clients weren't that receptive or into it after all?

Debra: So what's become de-emphasized, at least for now, is charitable giving review. We didn't get any takers on that. The Safe meeting, which we tried, which was, "Hey, something happens to you, where are all your documents, passwords?" trying to help people organize end-of-life stuff, that became a little de-emphasized. We're super excited about that. There's literally zero interest on that.

Michael: It's always fascinating between what's the industry buzz and what do clients actually show up for when you have a systematic way to ask them, and then you see what they do respond to and what they don't.

Debra: Yeah. Yeah. So we offered family retreat last year, and only one client took us up on that. And that's because they were having trouble. So it is interesting. And look, some of it is also education. People see it. They don't really understand what it means, how it would apply to them. And so part of, also, what we do, and this is where those announcements are so important that I talk about, the outreach, is part of our job is education and explaining to clients why this can be helpful to you. And so what you see is, over time, you don't get takers the first year. So then we'll review, and we'll be like, "Okay, we sent out this announcement offering to do a family retreat, and we thought at least these five or ten families would be interested. And they weren't. We heard nothing." So you're like, "All right. So, how are we going to look at this? Do we drop this? Do we telegraph it a different way? Do we actually call the clients and have a conversation about it?" So there is some game planning around this. And again, that's the dynamism, right? It's not a set-it-and-forget-it. It's just constantly evolving.

Michael: So now I've got to ask, at least briefly, because you mentioned it. What's the other magical thing you take into your prospect meetings that helps you close, your client service calendar and this one other thing? So, can I ask what the other magical thing is? Because most of us would like more $3 million to $6 million clients.

Debra: I know. You're great, Michael. It's this three-lane highway that I created.

Michael: Okay. What's the three-lane highway?

Debra: So basically, it is the piece that I use at every discovery meeting. I don't care if you have 2 million or 80 million. And basically, it is how we view wealth at Taylor Financial Group, my old firm, and now Carson Wealth. And it's three lanes. So imagine you just have it on a piece of paper, and the left lane is investment management. And I'm like, "That's what you're getting now. That's what you're doing for yourself. That's table stakes. And you're probably pretty pleased as how it's gone because you bought Microsoft or whatever."

Michael: And NVIDIA.

Debra: And NVIDIA, right. And usually, I introduce this after they've talked to me for 30 minutes, telling me what they're excited about, what keeps them up at night, what's important to them. So I let them talk for 30 or 40 minutes. I don't say anything. And I just keep asking questions. It's just very expository. And so I would just want to know everything, and so we just ask questions, ask questions, follow-ups, ask questions, and ask about the kids, the grandkids, all that stuff. And so I really get a picture of what their pain points are and all that. And then I pull out my three-lane highway. So sometimes it's literally 30 or 40 minutes in, and I've literally just said nothing about myself except asking them questions. So I'm like, "Okay, that's management. You're getting this. You're brilliant at it," or, "I know you're struggling with this a little bit. You're sitting on cash. You're worried about the market." So whatever it is, basically, repeating back what they just told me in the last 30 minutes. Okay. That's investment management. We do that.

And that's probably what you're used to people doing, and I'll literally cover the other two lanes. I'm like, "That's what you're used to doing." But let me talk to you about these other two lanes because this is where we really excel. So then the middle lane is financial planning. And I talk about financial planning in two ways, going on defense, going on offense. Defense is, will I outlive my money? I don't want to run out of money. And we know data shows us that that's the number one concern heading into retirement, regardless of how much money you have. So we say, "Okay, that's going on defense." But once we resolve that, and that's pretty easily resolved for our clients, because most clients are like you, they have $5 million, they have $10 million, so going on defense, yes, we need to address this.

But really, for many of our clients, it's going on offense. And offense is being creative. It's taking care of the people that we care about, our loved ones, and the causes we care about, and the community. And so, again, parroting back to them what's important to them, 529 for the grandkids, whatever it is, having a home in Naples. That's going on offense. That's living our dreams. And I tell them that's the most exciting part about my job, is we get to dream together. And they start lighting up.

And then this last lane, and the last lane is the family tax planning lane. And I call that the very lonely lane. And I tell them it's a lonely lane because it's tax planning, and most advisors don't do it, can't do it, aren't allowed to do it, don't have the software to do it. But we do it because it is so important for people like yourself. And so this is our specialty. I call it a lonely lane. We've always specialized in this. And I call it yeoman's work, and it's yeoman's work because it's highly customized to your situation. It's constantly changing. It's not scalable. And that's why other firms don't do it. But I don't feel comfortable as a professional not providing you the services that you need. And with $5 million and $4 million of it in a traditional IRA, you desperately need these services. And that's why we're here.

And so what we do, Mr. and Mrs. Prospect, is we integrate all of these services together for you to help drive down your lifetime taxes and build wealth for you and build wealth for your children and the next generation. That's basically the spiel. And I will tell you, that's my desert island piece. These two pieces, the three-lane highway, which I've used for over a decade, and then the service calendar, that's it. If I walk into a prospect meeting and I only have those two pieces, I close.

Michael: And is this also something you're comfortable to share just for people who want to see the visual of the highway or how you draw it out?

Debra: Sure.

Michael: Okay. Appreciate that. So again, then, for folks who are listening, this is episode 470. So if you go to kitces.com/470, I guess we'll have both of Debbie's two one-pagers, the three-lane highway, and how she walks into a prospect meeting with the service calendar.

So, Debbie, as you reflect on all this journey, what's surprised you the most about building your own advisory business over this career arc of 20-plus years?

Debra: How much work and how hard it is in certain ways.

Michael: So, are there particular parts? What hit you that you weren't expecting?

Debra: There's a lot of information. There's a lot of change in the industry. A lot of areas that you need to be thoughtful about if you're leading an advisory firm. And I think, to do it right, you need to roll up your sleeves and be willing to work very hard at it.

Michael: So, what was the low point for you?

Debra: I think one of the low points was 2015-2016, when I lost some of those large clients. I think another low point was '08-'09, to be honest. That was a really scary time to be in the business. I would tell you those are two low points. And then I think a third low-ish type point is when you lose a client that you've worked so hard for, and you thought you had a relationship and something that was real. And sometimes that's not how it works out.

Debra's Advice For Her Younger Self And For Newer Advisors [1:24:29]

Michael: So then, in retrospect, what do you know now you wish you could go back and teach younger you from a decade or two ago? What do you know now that you wish you knew back then?

Debra: I think having the right people around you is a total change maker. And so, years ago, I was just honestly hiring just so I could have a body in the door, and part of it also is I believe that they were as passionate about the business as I was. And so I made a lot of bad hiring decisions, and I think it creates a lot more work when you don't have the right people around you. In fairness, it's also hard to get the right people when you're a small, no-name firm, working in some suburban office place. So super hard, right? Nobody's like, "Yeah, I want to go work at wherever." So it's hard. But I'll tell you, taking the time to find the right people who are aligned, and so now, my entire team, we are aligned, we pull together, we have each other's backs, and it makes such a difference versus 10 or 15 years ago when I didn't have that.

Michael: Any other advice you would give younger, newer advisors coming into the profession today?

Debra: I think this is the best business/profession in the world. I am so grateful to be part of this profession. And I would say to young people, be willing to work hard at it and care for your clients the way you care for yourself, and you will have a very fulfilling and rewarding life that you can be very proud of.

Michael: What should they watch out for that they don't get fouled up on that journey?

Debra: I was reading in "The Wall Street Journal" this morning, even, and they were saying how young people are not dedicating themselves to their professions, that they are very focused on quality of life and had their work week at 41 hours. And, Michael, I don't think you've ever probably worked 41 hours, even when you're on vacation, probably.

Michael: A little guilty as charged there.

Debra: Yeah. And me, too, right? And so, look, life is a series of choices, and there are some choices that I've made that might not have been so great. I don't have a ton of hobbies. I don't have a billion friends. I've had to make choices because I have three children, and it's important to me to be a very good mother to them and also to be a great professional. And if you are a great professional and you're trying to be a great mother, there's not a lot of room left for happy hours with the girls and gardening, and all kinds of stuff. So I've had to make my share of sacrifices, too. And I'm not saying that they've got to follow the path that you followed, Michael, or that I followed, which some people might see as maybe a little extreme. But it's important to want to be great, and I think striving a little bit is very healthy. And so, for the young people out there, I think it's worth it to strive a little bit.

What Success Means To Debra [1:27:36]

Michael: So, as we come to the end, this is a podcast about success, and just one of the themes that comes up is that word success can mean very different things to different people. And so you've built this wonderfully successful firm as you're crossing half a billion dollars with this deep service model, and so the business seems to be in a wonderful place. How do you define success for yourself at this point?

Debra: I would say, success, Michael, is maybe a little bit more freedom. So I'm not sure what your schedule looks like, but I'm pretty busy these days. And, look, I like being busy. I choose to do this. I didn't have to be on your Intensive Tax CE Day, right? So, again, this is the path that I choose. But I do think success is starting to evolve a little bit, where maybe I learn how to lighten up just a tad.

Michael: Yep. Well, as the service calendar goes itself, sometimes we have seasons of life for ourselves when some priorities weigh higher in some seasons and some priorities shift as we move into different seasons.

Debra: Yes. Yeah. So maybe not saying yes to everything could be a version of success.

Michael: I love it. I love it, which is tough because that no word is really, really hard.

Debra: Yeah.

Michael: Well, very cool. Thank you so much, Debbie, for joining us on the "Financial Advisor Success" podcast.

Debra: Thank you. It's been a pleasure, Michael. The time has flown.

Michael: It has. It has. Thank you.